How to Weekend Like a Ferragamo

James Ferragamo shares his favorite pastimes in the Italian countryside.

Few names are as synonymous with Florence as Ferragamo, ever since Salvatore, a shoemaker, set up shop there in 1927, eventually moving headquarters to the 13th-century Palazzo Spini Feroni. Today the family, with nearly 100 members across four generations, stay connected at their estate near Chianti in Il Borro, a restored medieval village that encompasses a Relais & Châteaux hotel and villas. Salvatore’s grandson James, 49, who oversees shoes and leather goods for the company, loves exploring the region’s hill towns and lush coastline. Here’s how to spend a few days in his shoes:

Go hiking or hunting between meals, of course

“My father bought Il Borro in 1993, so I grew up there. I love returning to hunt with my father and my twin brother, Salvatore. Here, you can also ride horses, wander the countryside, and eat in small restaurants in villages like Poppi, where the Madonna del Morbo Sanctuary contains a painting of the Virgin attributed to Filippino Lippi, and Anghiari, full of ancient alleyways, arches, and ramparts that overlooked the famous Battle of Anghiari, all wonderfully intact.”

Be part of local tradition

“I love Arezzo and its ancient churches and squares. I’ll take a walk the first Sunday of every month through the antiques market (Fiera Antiquaria Di Arezzo) considered the largest in Italy. I’d also suggest a stroll to Piazza Grande, the most famous square in Arezzo, to see the Basilica di San Francesco, a medieval church dedicated to Saint Francis of Assisi. The Saracen Joust is a tournament that takes place in June and September in which locals wearing colorful costumes, horses accompanied by the town’s ancient banners, and the sound of trumpets create a festive medieval atmosphere. Afterward, you can have a relaxing lunch on the terrace under the loggia at Ristorante La Lancia D’Oro. Dessert is the best—just have whatever the chef proposes!”

Sail and swim along the Tuscan coast

“I love sailing in Roccamare, about two hours from Florence; it has a spectacular sea. Then there’s Castiglione della Pescaia, an enchanting seaside town in the heart of Maremma, whose pine woods extend from Punta Ala to the mountains of the Uccellina and along more than 99 miles of coastline, alternating between isolated coves and sandy stretches. Here, you can spend a whole day in the company of the famous butteri horsemen (or Tuscan cowboys), take a boat ride in the Diaccia Botrona nature reserve to see the ospreys and pink flamingos, or do a fishing trip with the fishermen of the Orbetello lagoon. I cherish these real experiences and the contact with nature.”